# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_12515_0m
_database_code_depnum_ccdc_archive 'CCDC 2333741'
loop_
_audit_author_name
_audit_author_address
'Liang ying'
;Southwest University of Science and Technology
China
;
_audit_update_record             
;
2024-11-08 deposited with the CCDC.	2024-11-21 downloaded from the CCDC.
;
_audit_creation_date             2024-11-08
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 H6 O S, C7 H6 N6 O4'
_chemical_formula_sum            'C9 H12 N6 O5 S'
_chemical_formula_weight         316.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   27.756(3)
_cell_length_b                   4.6794(5)
_cell_length_c                   19.632(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.257(4)
_cell_angle_gamma                90
_cell_volume                     2549.8(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1110
_cell_measurement_temperature    150.0(1)
_cell_measurement_theta_max      25.805
_cell_measurement_theta_min      2.536
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5034
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0976 before and 0.0719 after correction.
The Ratio of minimum to maximum transmission is 0.6753.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0984
_diffrn_reflns_av_unetI/netI     0.1032
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8229
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.422
_diffrn_reflns_theta_min         2.075
_diffrn_ambient_temperature      150.0(1)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1542
_reflns_number_total             2581
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2581
_refine_ls_number_restraints     178
_refine_ls_R_factor_all          0.1382
_refine_ls_R_factor_gt           0.0731
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0284P)²+17.5938P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1322
_refine_ls_wR_factor_ref         0.1669
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 S1A-C9A \\sim S1-C9
 with sigma of 0.001
 C8A-S1A \\sim C8-S1
 with sigma of 0.001
 C8A-S1A \\sim S1A-C9A
 with sigma of 0.001
 H8AA-O2 \\sim O2-H8AB
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C9) = Uanis(C9A)
Uanis(C8) = Uanis(C8A)
Uanis(S1) = Uanis(S1A)
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(S1A)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(H8AC)=Sof(C9A)=Sof(H9AA)=Sof(H9AB)=
 Sof(H9AC)=1-FVAR(1)
 Sof(S1)=Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(H8C)=Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(H9C)=
 FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C7(H7)
6.b X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N5(H5A,H5B)
6.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C8A(H8AA,H8AB,H8AC), C9A(H9AA,H9AB,H9AC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.56072(5) 0.9242(3) 0.59902(7) 0.0328(4) Uani 0.950(3) 1 d D U P A 1
O1 O 0.57237(12) 0.7177(8) 0.34287(17) 0.0356(9) Uani 1 1 d . U . . .
O2 O 0.58351(12) 0.7026(8) 0.45327(17) 0.0346(9) Uani 1 1 d D U . . .
O3 O 0.72096(11) -0.2643(7) 0.25946(15) 0.0288(8) Uani 1 1 d . U . . .
O4 O 0.67656(12) 0.0363(8) 0.20549(16) 0.0344(9) Uani 1 1 d . U . . .
O5 O 0.59513(12) 0.6793(8) 0.61264(17) 0.0361(8) Uani 1 1 d . U . . .
N1 N 0.62289(14) 0.3871(9) 0.26774(19) 0.0293(9) Uani 1 1 d . U . . .
H1A H 0.6308 0.3166 0.2278 0.035 Uiso 1 1 calc R . . . .
H1B H 0.6009 0.5218 0.2705 0.035 Uiso 1 1 calc R . . . .
N2 N 0.59449(14) 0.6130(9) 0.3948(2) 0.0266(8) Uani 1 1 d . U . . .
N3 N 0.64744(14) 0.3657(9) 0.51560(18) 0.0262(9) Uani 1 1 d . U . . .
H3 H 0.6276 0.4919 0.5334 0.031 Uiso 1 1 calc R . . . .
N4 N 0.70414(13) 0.0260(9) 0.51054(18) 0.0251(8) Uani 1 1 d . U . . .
N5 N 0.73897(13) -0.2199(9) 0.38731(19) 0.0277(9) Uani 1 1 d . U . . .
H5A H 0.7514 -0.2675 0.4270 0.033 Uiso 1 1 calc R . . . .
H5B H 0.7498 -0.2996 0.3498 0.033 Uiso 1 1 calc R . . . .
N6 N 0.69338(13) -0.0582(9) 0.26040(19) 0.0248(8) Uani 1 1 d . U . . .
C1 C 0.64423(15) 0.2901(10) 0.3240(2) 0.0219(9) Uani 1 1 d . U . . .
C2 C 0.62946(15) 0.4071(10) 0.3885(2) 0.0221(8) Uani 1 1 d . U . . .
C3 C 0.65258(15) 0.3022(10) 0.4481(2) 0.0220(9) Uani 1 1 d . U . . .
C4 C 0.68745(16) 0.0953(10) 0.4456(2) 0.0221(9) Uani 1 1 d . U . . .
C5 C 0.70404(16) -0.0289(10) 0.3840(2) 0.0226(9) Uani 1 1 d . U . . .
C6 C 0.68049(16) 0.0705(11) 0.3232(2) 0.0228(9) Uani 1 1 d . U . . .
C7 C 0.67899(16) 0.1954(11) 0.5499(2) 0.0269(10) Uani 1 1 d . U . . .
H7 H 0.6825 0.1990 0.5981 0.032 Uiso 1 1 calc R . . . .
C8 C 0.50451(16) 0.7709(13) 0.5791(3) 0.0385(11) Uani 0.950(3) 1 d D U P A 1
H8A H 0.5069 0.6655 0.5362 0.058 Uiso 0.950(3) 1 calc GR . P A 1
H8B H 0.4803 0.9221 0.5746 0.058 Uiso 0.950(3) 1 calc GR . P A 1
H8C H 0.4951 0.6397 0.6156 0.058 Uiso 0.950(3) 1 calc GR . P A 1
C9 C 0.5464(2) 1.0636(14) 0.6796(2) 0.0475(14) Uani 0.950(3) 1 d D U P A 1
H9A H 0.5374 0.9070 0.7103 0.071 Uiso 0.950(3) 1 calc GR . P A 1
H9B H 0.5193 1.1967 0.6752 0.071 Uiso 0.950(3) 1 calc GR . P A 1
H9C H 0.5744 1.1647 0.6983 0.071 Uiso 0.950(3) 1 calc GR . P A 1
S1A S 0.5422(9) 0.727(5) 0.6441(9) 0.0328(4) Uani 0.050(3) 1 d D U P A 2
C8A C 0.524(3) 0.825(17) 0.5613(13) 0.0385(11) Uani 0.050(3) 1 d D U P A 2
H8AA H 0.5199 1.0331 0.5591 0.058 Uiso 0.050(3) 1 calc DGR . P A 2
H8AB H 0.4938 0.7307 0.5499 0.058 Uiso 0.050(3) 1 calc DGR . P A 2
H8AC H 0.5490 0.7672 0.5287 0.058 Uiso 0.050(3) 1 calc GR . P A 2
C9A C 0.522(3) 0.999(8) 0.699(2) 0.0475(14) Uani 0.050(3) 1 d D U P A 2
H9AA H 0.5498 1.0999 0.7182 0.071 Uiso 0.050(3) 1 calc GR . P A 2
H9AB H 0.5031 0.9138 0.7358 0.071 Uiso 0.050(3) 1 calc GR . P A 2
H9AC H 0.5019 1.1334 0.6733 0.071 Uiso 0.050(3) 1 calc GR . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O5 1.515(4) . ?
S1 C8 1.759(4) . ?
S1 C9 1.759(4) . ?
O1 N2 1.284(5) . ?
O2 N2 1.262(5) . ?
O3 N6 1.231(5) . ?
O4 N6 1.254(5) . ?
O5 S1A 1.61(2) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N1 C1 1.331(5) . ?
N2 C2 1.374(6) . ?
N3 H3 0.8800 . ?
N3 C3 1.366(6) . ?
N3 C7 1.360(6) . ?
N4 C4 1.393(5) . ?
N4 C7 1.311(6) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N5 C5 1.320(6) . ?
N6 C6 1.420(6) . ?
C1 C2 1.440(6) . ?
C1 C6 1.438(6) . ?
C2 C3 1.421(6) . ?
C3 C4 1.370(6) . ?
C4 C5 1.419(6) . ?
C5 C6 1.435(6) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
S1A C8A 1.759(4) . ?
S1A C9A 1.759(4) . ?
C8A H8AA 0.9800 . ?
C8A H8AB 0.9800 . ?
C8A H8AC 0.9800 . ?
C9A H9AA 0.9800 . ?
C9A H9AB 0.9800 . ?
C9A H9AC 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 S1 C8 106.8(3) . . ?
O5 S1 C9 105.5(3) . . ?
C9 S1 C8 98.4(3) . . ?
H1A N1 H1B 120.0 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
O1 N2 C2 122.1(4) . . ?
O2 N2 O1 118.6(4) . . ?
O2 N2 C2 119.3(4) . . ?
C3 N3 H3 126.8 . . ?
C7 N3 H3 126.8 . . ?
C7 N3 C3 106.4(4) . . ?
C7 N4 C4 102.9(4) . . ?
H5A N5 H5B 120.0 . . ?
C5 N5 H5A 120.0 . . ?
C5 N5 H5B 120.0 . . ?
O3 N6 O4 119.5(4) . . ?
O3 N6 C6 120.3(4) . . ?
O4 N6 C6 120.2(4) . . ?
N1 C1 C2 118.2(4) . . ?
N1 C1 C6 123.0(4) . . ?
C6 C1 C2 118.8(4) . . ?
N2 C2 C1 123.3(4) . . ?
N2 C2 C3 119.0(4) . . ?
C3 C2 C1 117.6(4) . . ?
N3 C3 C2 132.5(4) . . ?
N3 C3 C4 105.5(4) . . ?
C4 C3 C2 122.0(4) . . ?
N4 C4 C5 125.2(4) . . ?
C3 C4 N4 111.3(4) . . ?
C3 C4 C5 123.5(4) . . ?
N5 C5 C4 118.4(4) . . ?
N5 C5 C6 126.3(4) . . ?
C4 C5 C6 115.3(4) . . ?
N6 C6 C1 119.4(4) . . ?
N6 C6 C5 118.0(4) . . ?
C5 C6 C1 122.6(4) . . ?
N3 C7 H7 123.0 . . ?
N4 C7 N3 113.9(4) . . ?
N4 C7 H7 123.0 . . ?
S1 C8 H8A 109.5 . . ?
S1 C8 H8B 109.5 . . ?
S1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
S1 C9 H9A 109.5 . . ?
S1 C9 H9B 109.5 . . ?
S1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O5 S1A C8A 86(3) . . ?
O5 S1A C9A 129(3) . . ?
C8A S1A C9A 107(3) . . ?
S1A C8A H8AA 109.5 . . ?
S1A C8A H8AB 109.5 . . ?
S1A C8A H8AC 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
S1A C9A H9AA 109.5 . . ?
S1A C9A H9AB 109.5 . . ?
S1A C9A H9AC 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_submission_special_instructions 'No special instructions were received'
